New approach toward the synthesis of deuterated pyrazolo[1,5-a]pyridines and 1,2,4-triazolo[1,5-a]pyridines

An efficient and operationally simple synthesis of 7-deuteropyrazolo[1,5-a]pyridine and 7-deutero-1,2,4-triazolo[1,5-a]pyridine derivatives using α-H/D exchange of 1-aminopyridinium cations in basic D(2)O followed by a 1,3-cycloaddition of acetylenes and nitriles is presented. A high regioselectivit...

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Autores principales: Vorob’ev, Aleksey Yu, Supranovich, Vyacheslav I, Borodkin, Gennady I, Shubin, Vyacheslav G
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5433178/
https://www.ncbi.nlm.nih.gov/pubmed/28546837
http://dx.doi.org/10.3762/bjoc.13.80
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author Vorob’ev, Aleksey Yu
Supranovich, Vyacheslav I
Borodkin, Gennady I
Shubin, Vyacheslav G
author_facet Vorob’ev, Aleksey Yu
Supranovich, Vyacheslav I
Borodkin, Gennady I
Shubin, Vyacheslav G
author_sort Vorob’ev, Aleksey Yu
collection PubMed
description An efficient and operationally simple synthesis of 7-deuteropyrazolo[1,5-a]pyridine and 7-deutero-1,2,4-triazolo[1,5-a]pyridine derivatives using α-H/D exchange of 1-aminopyridinium cations in basic D(2)O followed by a 1,3-cycloaddition of acetylenes and nitriles is presented. A high regioselectivity and a high degree of deuterium incorporation were achieved. The procedure was applied for several 4-R-1-aminopyridinium cations (R = H, Me, OMe).
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spelling pubmed-54331782017-05-25 New approach toward the synthesis of deuterated pyrazolo[1,5-a]pyridines and 1,2,4-triazolo[1,5-a]pyridines Vorob’ev, Aleksey Yu Supranovich, Vyacheslav I Borodkin, Gennady I Shubin, Vyacheslav G Beilstein J Org Chem Full Research Paper An efficient and operationally simple synthesis of 7-deuteropyrazolo[1,5-a]pyridine and 7-deutero-1,2,4-triazolo[1,5-a]pyridine derivatives using α-H/D exchange of 1-aminopyridinium cations in basic D(2)O followed by a 1,3-cycloaddition of acetylenes and nitriles is presented. A high regioselectivity and a high degree of deuterium incorporation were achieved. The procedure was applied for several 4-R-1-aminopyridinium cations (R = H, Me, OMe). Beilstein-Institut 2017-05-02 /pmc/articles/PMC5433178/ /pubmed/28546837 http://dx.doi.org/10.3762/bjoc.13.80 Text en Copyright © 2017, Vorob’ev et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Vorob’ev, Aleksey Yu
Supranovich, Vyacheslav I
Borodkin, Gennady I
Shubin, Vyacheslav G
New approach toward the synthesis of deuterated pyrazolo[1,5-a]pyridines and 1,2,4-triazolo[1,5-a]pyridines
title New approach toward the synthesis of deuterated pyrazolo[1,5-a]pyridines and 1,2,4-triazolo[1,5-a]pyridines
title_full New approach toward the synthesis of deuterated pyrazolo[1,5-a]pyridines and 1,2,4-triazolo[1,5-a]pyridines
title_fullStr New approach toward the synthesis of deuterated pyrazolo[1,5-a]pyridines and 1,2,4-triazolo[1,5-a]pyridines
title_full_unstemmed New approach toward the synthesis of deuterated pyrazolo[1,5-a]pyridines and 1,2,4-triazolo[1,5-a]pyridines
title_short New approach toward the synthesis of deuterated pyrazolo[1,5-a]pyridines and 1,2,4-triazolo[1,5-a]pyridines
title_sort new approach toward the synthesis of deuterated pyrazolo[1,5-a]pyridines and 1,2,4-triazolo[1,5-a]pyridines
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5433178/
https://www.ncbi.nlm.nih.gov/pubmed/28546837
http://dx.doi.org/10.3762/bjoc.13.80
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